(E)-1-Phenyl­ethanone semicarbazone

Fun, H.-K.; Yeap, C.S.; Padaki, M.; Malladi, S.; Isloor, A.M.

doi:10.1107/S1600536809025847

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Pages o1807-o1808

doi:10.1107/S1600536809025847

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(E)-1-Phenylethanone semicarbazone

Hoong-Kun Fun,^a ^*‡ Chin Sing Yeap,^a § Mahesh Padaki,^b Shridhar Malladi ^b and Arun M Isloor ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India
^*Correspondence e-mail: hkfun@usm.my

(Received 26 June 2009; accepted 3 July 2009; online 11 July 2009)

In the title compound, C₉H₁₁N₃O, the benzene ring is disordered over two positions with refined occupancies of 0.922 (5) and 0.078 (5). The program PLATON [Spek (2009 ). Acta Cryst. D65, 148–155] recommends the solution in the space group C2/m with a = 7.3050 (3), b = 6.6745 (2), c = 18.3853 (6) Å and β = 96.986 (2)°. However, the large number of non-extinct reflections needed to be ignored if C2/m is chosen suggested that the space group is incorrect, even though the R values are lower than that for P2₁/c. The semicarbazone group is essentially planar, with a maximum deviation of 0.046 (1) Å for one of the N atoms. The mean plane of the semicarbazone group forms dihedral angles of 33.61 (8) and 39.1 (9)° with the benzene ring of the major and minor components, respectively. In the crystal structure, molecules are linked by intermolecular N—H⋯O hydrogen bonds into extended chains along the c axis. The crystal structure is further stabilized by weak intermolucular C—H⋯π interactions.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For applications of semicarbazone derivatives, see: Chandra & Gupta (2005 ); Jain et al. (2002 ); Pilgram (1978 ); Warren et al. (1977 ); Yogeeswari et al. (2004 ). For the preparation of the title compound, see: Furniss et al. (1978 ). For related structures, see: Fun et al. (2009a ,b ,c ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₉H₁₁N₃O
M_r = 177.21
Monoclinic, P 2₁ /c
a = 18.3853 (6) Å
b = 6.6745 (2) Å
c = 7.3050 (3) Å
β = 96.986 (2)°
V = 889.76 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.32 × 0.13 × 0.03 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.881, T_max = 0.997
9294 measured reflections
2034 independent reflections
1449 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.181
S = 1.08
2034 reflections
148 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O1ⁱ	0.88 (3)	2.02 (3)	2.901 (3)	177.2 (19)
N3—H2N3⋯O1ⁱⁱ	0.86 (3)	2.04 (3)	2.894 (3)	173 (3)
C2A—H2AA⋯Cgⁱⁱⁱ	0.93	2.93	3.707 (2)	142
C5A—H5AA⋯Cg^iv	0.93	2.90	3.678 (2)	142
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x+1, -y+1, -z+1; (iii) $[x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ ; (iv) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ . Cg is the centroid of the C1A,C2A,C3,C4A,C5A,C6 benzene ring.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809025847/lh2857sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809025847/lh2857Isup2.hkl

checkCIF report

Comment top

In organic chemistry, a semicarbazone is a derivative of an aldehyde or ketone formed by a condensation between a ketone or aldehyde and semicarbazide. Semicarbazone find immense applications in the field of synthetic chemistry, such as medicinal chemistry (Warren et al., 1977), organometalics (Chandra & Gupta, 2005), polymers (Jain et al., 2002) and herbicides (Pilgram, 1978). 4-Sulphamoylphenyl semicarbazones were synthesized and were found to possess anticonvulsant activity (Yogeeswari et al., 2004). We hereby report the crystal structure of a semicarbazone of potential commercial importance, (I).

The bond lengths and angles of the title compound (I), (Fig. 1) are comparable to related structures (Fun et al., 2009a, b, c). A maximum deviation of -0.046 (1) Å for atom N2 from atoms O1, N1, N2, N3, C6, C7, C8 and C9 indicates that the semicarbazone group is essentially coplanar. This mean plane makes dihedral angle of 33.61 (8) and 39.1 (9)° with benzene ring of the major and minor component (C1A-C2A-C3-C4A-C5A-C6 and C1B-C2B-C3-C4B-C5B-C6), respectively. The molecules are linked together into infinite one-dimensional chains by the intermolecular N2—H1N2···O1ⁱ and N3—H2N3···O1ⁱⁱ (see Table 1 for symmetry codes) hydrogen bonds along the c axis (Fig. 2) and these hydrogen bonds generate R₂²(8) ring motifs (Bernstein et al., 1995). The crystal structure is stabilized by the weak intermolucular C—H···π interactions (Table 1).

Related literature top

For hydrogen-bond motifs, see: Bernstein et al. (1995). For applications of semicarbazone derivatives, see: Chandra & Gupta (2005); Jain et al. (2002); Pilgram (1978); Warren et al. (1977); Yogeeswari et al. (2004). For the preparation of the title compound, see: Furniss et al. (1978). For related structures, see: Fun et al. (2009a,b,c). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986). Cg is the centroid of C1A,C2A,C3,C4A,C5A,C6 benzene ring.

Experimental top

Semicarbazide hydrochloride (1.0 g, 8.9 mmol) and freshly recrystallized sodium acetate (0.9 g, 10.9 mmol) were dissolved in water (10 ml) following a literature procedure (Furniss et al., 1978). The reaction mixture was stirred at room temperature for 10 minutes. To this, (1.0 g, 8.32 mmol) acetophenone was added and shaken well. A little alcohol was added to dissolve the turbidity. It was shaken for 10 more minutes and allowed to stand. The semicarbazone crystallizes on standing for 6 h. The separated crystals were filtered, washed with cold water and recrystallized from alcohol. Yield: 1.37 g (93%). M.p. 473-478 K.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with atom labels and 50% probability ellipsoids for non-H atoms. All disorder components are shown. The minor disorder component is shown with open bonds.
	Fig. 2. Part of the crystal structure of (I), viewed along the b axis. Intermolecular hydrogen bonds are shown in as dashed lines. Only the major disorder component is shown.

(E)-1-Phenylethanone semicarbazone top

Crystal data top

C₉H₁₁N₃O	F(000) = 376
M_r = 177.21	D_x = 1.323 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2113 reflections
a = 18.3853 (6) Å	θ = 3.4–29.6°
b = 6.6745 (2) Å	µ = 0.09 mm⁻¹
c = 7.3050 (3) Å	T = 100 K
β = 96.986 (2)°	Plate, colourless
V = 889.76 (5) Å³	0.32 × 0.13 × 0.03 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2034 independent reflections
Radiation source: fine-focus sealed tube	1449 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
ϕ and ω scans	θ_max = 27.5°, θ_min = 1.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −23→23
T_min = 0.881, T_max = 0.997	k = −8→8
9294 measured reflections	l = −5→9

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.181	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0993P)² + 0.2822P] where P = (F_o² + 2F_c²)/3
2034 reflections	(Δ/σ)_max < 0.001
148 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

C₉H₁₁N₃O	V = 889.76 (5) Å³
M_r = 177.21	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 18.3853 (6) Å	µ = 0.09 mm⁻¹
b = 6.6745 (2) Å	T = 100 K
c = 7.3050 (3) Å	0.32 × 0.13 × 0.03 mm
β = 96.986 (2)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2034 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1449 reflections with I > 2σ(I)
T_min = 0.881, T_max = 0.997	R_int = 0.043
9294 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.181	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.43 e Å⁻³
2034 reflections	Δρ_min = −0.46 e Å⁻³
148 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.51345 (7)	0.4963 (2)	0.7657 (2)	0.0165 (4)
N1	0.32789 (9)	0.4925 (2)	0.8239 (3)	0.0130 (4)
N2	0.40259 (9)	0.4938 (2)	0.8715 (3)	0.0142 (4)
N3	0.41052 (10)	0.4917 (3)	0.5585 (3)	0.0174 (5)
C3	0.05611 (11)	0.5011 (3)	0.7581 (3)	0.0169 (5)
H3A	0.0064	0.5007	0.7151	0.020*
C6	0.20605 (10)	0.5016 (3)	0.8879 (3)	0.0114 (4)
C7	0.28592 (11)	0.5045 (3)	0.9528 (3)	0.0119 (5)
C8	0.44581 (11)	0.4942 (3)	0.7296 (3)	0.0135 (5)
C9	0.31370 (11)	0.5196 (3)	1.1541 (3)	0.0149 (5)
H9A	0.3444	0.6357	1.1750	0.022*
H9B	0.3415	0.4018	1.1920	0.022*
H9C	0.2730	0.5311	1.2242	0.022*
C1A	0.17941 (11)	0.3969 (3)	0.7290 (3)	0.0144 (5)	0.922 (5)
H1AA	0.2120	0.3267	0.6649	0.017*	0.922 (5)
C2A	0.10550 (12)	0.3954 (3)	0.6644 (3)	0.0176 (5)	0.922 (5)
H2AA	0.0888	0.3238	0.5584	0.021*	0.922 (5)
C4A	0.08190 (11)	0.6070 (3)	0.9162 (3)	0.0164 (5)	0.922 (5)
H4AA	0.0492	0.6784	0.9789	0.020*	0.922 (5)
C5A	0.15600 (11)	0.6073 (3)	0.9816 (3)	0.0142 (5)	0.922 (5)
H5AA	0.1726	0.6781	1.0883	0.017*	0.922 (5)
C1B	0.1548 (15)	0.395 (4)	0.979 (4)	0.022 (7)*	0.078 (5)
H1BA	0.1725	0.3268	1.0861	0.026*	0.078 (5)
C2B	0.0822 (18)	0.385 (5)	0.923 (5)	0.032 (8)*	0.078 (5)
H2BA	0.0506	0.3096	0.9861	0.039*	0.078 (5)
C4B	0.1048 (17)	0.607 (5)	0.664 (5)	0.032 (8)*	0.078 (5)
H4BA	0.0876	0.6756	0.5570	0.038*	0.078 (5)
C5B	0.1785 (16)	0.612 (5)	0.728 (4)	0.025 (7)*	0.078 (5)
H5BA	0.2103	0.6871	0.6662	0.030*	0.078 (5)
H1N2	0.4271 (15)	0.500 (3)	0.983 (4)	0.025 (7)*
H1N3	0.3627 (14)	0.495 (3)	0.543 (4)	0.019 (6)*
H2N3	0.4366 (14)	0.496 (3)	0.469 (4)	0.020 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0110 (7)	0.0241 (8)	0.0143 (8)	−0.0017 (6)	0.0015 (6)	−0.0005 (6)
N1	0.0088 (8)	0.0142 (8)	0.0159 (9)	0.0007 (6)	0.0010 (6)	−0.0003 (7)
N2	0.0094 (8)	0.0207 (9)	0.0121 (9)	−0.0008 (7)	−0.0002 (7)	0.0002 (8)
N3	0.0102 (9)	0.0303 (11)	0.0118 (9)	−0.0010 (8)	0.0020 (7)	0.0001 (8)
C3	0.0101 (9)	0.0172 (10)	0.0227 (12)	0.0015 (8)	−0.0007 (8)	0.0033 (9)
C6	0.0110 (9)	0.0101 (9)	0.0131 (10)	0.0001 (7)	0.0008 (7)	0.0028 (8)
C7	0.0131 (9)	0.0088 (9)	0.0135 (10)	0.0005 (7)	0.0006 (8)	0.0005 (8)
C8	0.0121 (9)	0.0133 (9)	0.0152 (10)	0.0000 (7)	0.0024 (7)	−0.0005 (8)
C9	0.0118 (9)	0.0243 (11)	0.0086 (10)	−0.0009 (8)	0.0016 (7)	−0.0015 (8)
C1A	0.0135 (10)	0.0140 (11)	0.0155 (12)	0.0018 (8)	0.0015 (9)	−0.0016 (9)
C2A	0.0158 (11)	0.0169 (11)	0.0189 (12)	−0.0007 (9)	−0.0028 (9)	−0.0009 (9)
C4A	0.0127 (11)	0.0186 (12)	0.0185 (12)	0.0018 (9)	0.0045 (9)	−0.0008 (9)
C5A	0.0160 (11)	0.0143 (11)	0.0120 (11)	0.0012 (9)	0.0011 (8)	−0.0008 (9)

Geometric parameters (Å, º) top

O1—C8	1.240 (2)	C6—C7	1.487 (3)
N1—C7	1.290 (3)	C7—C9	1.500 (3)
N1—N2	1.375 (2)	C9—H9A	0.9600
N2—C8	1.380 (3)	C9—H9B	0.9600
N2—H1N2	0.88 (3)	C9—H9C	0.9600
N3—C8	1.336 (3)	C1A—C2A	1.383 (3)
N3—H1N3	0.87 (3)	C1A—H1AA	0.9300
N3—H2N3	0.85 (3)	C2A—H2AA	0.9300
C3—C4B	1.39 (3)	C4A—C5A	1.388 (3)
C3—C4A	1.387 (3)	C4A—H4AA	0.9300
C3—C2A	1.394 (3)	C5A—H5AA	0.9300
C3—C2B	1.46 (3)	C1B—C2B	1.35 (4)
C3—H3A	0.9300	C1B—H1BA	0.9300
C6—C1A	1.392 (3)	C2B—H2BA	0.9300
C6—C5A	1.402 (3)	C4B—C5B	1.38 (4)
C6—C1B	1.41 (3)	C4B—H4BA	0.9300
C6—C5B	1.42 (3)	C5B—H5BA	0.9300

C7—N1—N2	118.86 (18)	N3—C8—N2	116.34 (18)
N1—N2—C8	117.31 (18)	C7—C9—H9A	109.5
N1—N2—H1N2	128.1 (18)	C7—C9—H9B	109.5
C8—N2—H1N2	114.6 (18)	H9A—C9—H9B	109.5
C8—N3—H1N3	119.0 (17)	C7—C9—H9C	109.5
C8—N3—H2N3	117.3 (18)	H9A—C9—H9C	109.5
H1N3—N3—H2N3	124 (2)	H9B—C9—H9C	109.5
C4B—C3—C4A	88.6 (14)	C2A—C1A—C6	121.3 (2)
C4B—C3—C2A	61.1 (13)	C2A—C1A—H1AA	119.4
C4A—C3—C2A	119.32 (19)	C6—C1A—H1AA	119.4
C4B—C3—C2B	120.7 (19)	C1A—C2A—C3	120.0 (2)
C4A—C3—C2B	62.5 (13)	C1A—C2A—H2AA	120.0
C2A—C3—C2B	88.3 (13)	C3—C2A—H2AA	120.0
C4B—C3—H3A	120.2	C3—C4A—C5A	120.6 (2)
C4A—C3—H3A	120.3	C3—C4A—H4AA	119.7
C2A—C3—H3A	120.3	C5A—C4A—H4AA	119.7
C2B—C3—H3A	119.1	C4A—C5A—C6	120.4 (2)
C1A—C6—C5A	118.32 (18)	C4A—C5A—H5AA	119.8
C1A—C6—C1B	87.4 (12)	C6—C5A—H5AA	119.8
C5A—C6—C1B	60.4 (11)	C2B—C1B—C6	125 (3)
C1A—C6—C5B	61.3 (12)	C2B—C1B—H1BA	117.4
C5A—C6—C5B	87.2 (12)	C6—C1B—H1BA	117.4
C1B—C6—C5B	117.2 (17)	C1B—C2B—C3	116 (3)
C1A—C6—C7	120.39 (17)	C1B—C2B—H2BA	122.1
C5A—C6—C7	121.27 (19)	C3—C2B—H2BA	122.1
C1B—C6—C7	123.1 (12)	C5B—C4B—C3	121 (3)
C5B—C6—C7	119.7 (12)	C5B—C4B—H4BA	119.6
N1—C7—C6	114.93 (18)	C3—C4B—H4BA	119.6
N1—C7—C9	123.85 (18)	C4B—C5B—C6	120 (3)
C6—C7—C9	121.22 (17)	C4B—C5B—H5BA	119.9
O1—C8—N3	124.04 (19)	C6—C5B—H5BA	119.9
O1—C8—N2	119.63 (19)

C7—N1—N2—C8	−175.79 (18)	C2B—C3—C4A—C5A	70.3 (14)
N2—N1—C7—C6	−179.91 (16)	C3—C4A—C5A—C6	0.5 (3)
N2—N1—C7—C9	−0.2 (3)	C1A—C6—C5A—C4A	−0.1 (3)
C1A—C6—C7—N1	30.7 (3)	C1B—C6—C5A—C4A	−68.7 (14)
C5A—C6—C7—N1	−147.66 (19)	C5B—C6—C5A—C4A	54.9 (12)
C1B—C6—C7—N1	139.4 (14)	C7—C6—C5A—C4A	178.31 (19)
C5B—C6—C7—N1	−41.4 (14)	C1A—C6—C1B—C2B	−54 (3)
C1A—C6—C7—C9	−149.0 (2)	C5A—C6—C1B—C2B	71 (3)
C5A—C6—C7—C9	32.6 (3)	C5B—C6—C1B—C2B	2 (4)
C1B—C6—C7—C9	−40.4 (14)	C7—C6—C1B—C2B	−179 (2)
C5B—C6—C7—C9	138.9 (14)	C6—C1B—C2B—C3	−2 (4)
N1—N2—C8—O1	179.65 (17)	C4B—C3—C2B—C1B	2 (4)
N1—N2—C8—N3	−0.5 (3)	C4A—C3—C2B—C1B	−68 (2)
C5A—C6—C1A—C2A	−0.3 (3)	C2A—C3—C2B—C1B	57 (3)
C1B—C6—C1A—C2A	53.8 (12)	C4A—C3—C4B—C5B	54 (3)
C5B—C6—C1A—C2A	−69.3 (13)	C2A—C3—C4B—C5B	−71 (3)
C7—C6—C1A—C2A	−178.78 (19)	C2B—C3—C4B—C5B	−2 (4)
C6—C1A—C2A—C3	0.4 (3)	C3—C4B—C5B—C6	2 (4)
C4B—C3—C2A—C1A	69.9 (17)	C1A—C6—C5B—C4B	68 (3)
C4A—C3—C2A—C1A	−0.1 (3)	C5A—C6—C5B—C4B	−57 (3)
C2B—C3—C2A—C1A	−57.0 (13)	C1B—C6—C5B—C4B	−2 (3)
C4B—C3—C4A—C5A	−55.7 (14)	C7—C6—C5B—C4B	179 (2)
C2A—C3—C4A—C5A	−0.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1ⁱ	0.88 (3)	2.02 (3)	2.901 (3)	177.2 (19)
N3—H2N3···O1ⁱⁱ	0.86 (3)	2.04 (3)	2.894 (3)	173 (3)
C2A—H2AA···Cgⁱⁱⁱ	0.93	2.93	3.707 (2)	142
C5A—H5AA···Cg^iv	0.93	2.90	3.678 (2)	142

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+1, −y+1, −z+1; (iii) x, −y−1/2, z−3/2; (iv) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₉H₁₁N₃O
M_r	177.21
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	18.3853 (6), 6.6745 (2), 7.3050 (3)
β (°)	96.986 (2)
V (Å³)	889.76 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.32 × 0.13 × 0.03

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.881, 0.997
No. of measured, independent and observed [I > 2σ(I)] reflections	9294, 2034, 1449
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.181, 1.08
No. of reflections	2034
No. of parameters	148
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.46

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1ⁱ	0.88 (3)	2.02 (3)	2.901 (3)	177.2 (19)
N3—H2N3···O1ⁱⁱ	0.86 (3)	2.04 (3)	2.894 (3)	173 (3)
C2A—H2AA···Cgⁱⁱⁱ	0.9300	2.93	3.707 (2)	142
C5A—H5AA···Cg^iv	0.9300	2.90	3.678 (2)	142

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+1, −y+1, −z+1; (iii) x, −y−1/2, z−3/2; (iv) x, −y+1/2, z−1/2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5523-2009.

Acknowledgements

HKF thanks Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012. CSY thanks the Malaysian Government and Universiti Sains Malaysia for the award of the post of Research Officer under the Science Fund grant No. 305/PFIZIK/613312. AMI is grateful to the Head of the Department of Chemistry and the Director, NITK, Surathkal, India, for providing research facilities.

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